DE4440328A1 - Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides - Google Patents
Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amidesInfo
- Publication number
- DE4440328A1 DE4440328A1 DE4440328A DE4440328A DE4440328A1 DE 4440328 A1 DE4440328 A1 DE 4440328A1 DE 4440328 A DE4440328 A DE 4440328A DE 4440328 A DE4440328 A DE 4440328A DE 4440328 A1 DE4440328 A1 DE 4440328A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- amphiphilic compounds
- compounds according
- spacer
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 125000001165 hydrophobic group Chemical group 0.000 title abstract description 7
- 150000001408 amides Chemical class 0.000 title abstract description 3
- 125000006850 spacer group Chemical group 0.000 claims abstract description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- 238000004140 cleaning Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 4
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 3
- 238000005555 metalworking Methods 0.000 claims abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract 4
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 claims description 13
- 150000004703 alkoxides Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000006384 oligomerization reaction Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- 238000005065 mining Methods 0.000 claims 2
- 239000004753 textile Substances 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- -1 demulsifiers Substances 0.000 abstract description 34
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003599 detergent Substances 0.000 abstract description 2
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 230000003165 hydrotropic effect Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000004381 surface treatment Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JBVOQKNLGSOPNZ-UHFFFAOYSA-N 2-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC=CC=C1S(O)(=O)=O JBVOQKNLGSOPNZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005640 Methyl decanoate Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229960003872 benzethonium Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229940071118 cumenesulfonate Drugs 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000003549 soybean oil Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Materials Engineering (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
Die Erfindung betrifft amphiphile Verbindungen mit mindestens zwei hydro philen und mindestens zwei hydrophoben Gruppen auf der Basis von Amiden.The invention relates to amphiphilic compounds with at least two hydro philes and at least two hydrophobic groups based on amides.
Als amphiphile Substanzen sind eine große Vielfalt an anionischen, katio nischen, nichtionischen und zwitterionischen Verbindungen bekannt. Die weitaus meisten dieser Substanzen bestehen aus einer hydrophilen Kopf gruppe und wenigstens einem hydrophoben Teil.A wide variety of anionic, katio are as amphiphilic substances African, nonionic and zwitterionic compounds known. The By far most of these substances consist of a hydrophilic head group and at least one hydrophobic part.
Bei den amphiphilen Substanzen gibt es aus ökologischen Gründen, z. B. bezüglich der Verringerung des Verpackungs- und Transportaufwandes, die Notwendigkeit, immer größere Wirkung pro Masse an eingesetzter Substanz zu erzielen. Da eine Optimierung durch Mischung von amphiphilen Substanzen nur sehr begrenzt weiterführt, sind neue amphiphile Substanzen mit einem höheren Wirkungsgrad erforderlich. Es müssen daher insbesondere Stoffe mit niedrigeren kritischen Micellbildungskonzentrationen und/oder niedrigeren Ober- und Grenzflächenspannungen gefunden werden, um die Ein satzmengen an Wirksubstanz deutlich reduzieren zu können.In the case of amphiphilic substances, there are ecological reasons, e.g. B. with regard to the reduction of packaging and transport costs, the Necessity, ever greater effect per mass of substance used to achieve. Because an optimization by mixing amphiphilic substances only continues to a very limited extent, are new amphiphilic substances higher efficiency is required. It must therefore be particularly Substances with lower critical micelle formation concentrations and / or lower surface and interfacial tensions can be found around the A to be able to significantly reduce the amount of active substance.
Erste Lösungsansätze in dieser Richtung durch Verkoppelung eines Teils der Struktur (hydrophile Kopfgruppe, hydrophobe Gruppe) sind bereits be kannt. So können kationische grenzflächenaktive Verbindungen durch die Addition von langkettigen Alkylhalogeniden an permethylierte Alkylendi amine erhalten werden [R. Zana, M. Benrraou, R. Rueff, Langmuir, 7 (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alamin, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].First approaches in this direction by coupling a part the structure (hydrophilic head group, hydrophobic group) are already be knows. Cationic surfactant compounds can thus be Addition of long chain alkyl halides to permethylated alkylene di amines are obtained [R. Zana, M. Benrraou, R. Rueff, Langmuir, 7 (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alamin, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].
Anionische grenzflächenaktive Verbindungen mit wenigstens zwei hydrophilen und wenigstens zwei hydrophoben Gruppen sind bisher nur auf der Basis von Diglycidylethern hergestellt worden (US 5 160 450, JP 01 304 033, JP 4 124 165). Diglycidylether gelten jedoch als toxikologisch bedenklich und sich recht teuer. Darüber hinaus wird für ihre Herstellung Epichlor hydrin verwendet, was zu großen Mengen an Reststoffen führt, so daß diese Verbindungen unter ökotoxikologischen wie auch ökonomischen Gesichtspunkten nicht mehr zeitgemäß sind.Anionic surfactant compounds with at least two hydrophilic and at least two hydrophobic groups have so far only been based of diglycidyl ethers (US 5 160 450, JP 01 304 033, JP 4 124 165). However, diglycidyl ethers are considered toxicologically unsafe and become quite expensive. In addition, Epichlor is used for their manufacture hydrin used, which leads to large amounts of residues, so this Connections from an ecotoxicological as well as an economic point of view are out of date.
Es bestand daher die Aufgabe, amphiphile Verbindungen aufzufinden, die wenigstens zwei hydrophile und wenigstens zwei hydrophobe Gruppen aufweisen, wobei die amphiphilen Verbindungen einen sehr hohen Wirkungsgrad, bezogen auf die Einsatzmenge, haben, und die darüber hinaus aus technisch leicht verfügbaren Rohstoffen ohne großen Anfall von unerwünschten Neben produkten hergestellt werden können.The task was therefore to find amphiphilic compounds that have at least two hydrophilic and at least two hydrophobic groups, the amphiphilic compounds being very efficient, based on the amount used, and also from a technical point of view readily available raw materials without a large amount of unwanted addition products can be manufactured.
Die Aufgabe wird erfindungsgemäß durch amphiphile Di- oder Oligoamide, deren Grundkörper aus Di- oder Oligoaminen und Fettsäuren bzw. Fettsäure methylestern hergestellt werden können, gelöst. Die entsprechenden Di- oder Oligoamide können alkoxyliert werden. Diese nichtionischen amphiphilen Verbindungen können in anionische amphiphile Verbindungen überführt werden, indem man z. B. die vorgenannten Verbindungen mit SO₃/Inertgas (oder Oleum oder Chlorsulfonsäure), mit Polyphosphorsäure, mit einer Halogenessigsäure, mit einem Sulton oder mit einem Taurin, umsetzt und jeweils anschließend neutralisiert.According to the invention, the object is achieved by amphiphilic di- or oligoamides, the basic body of di- or oligoamines and fatty acids or fatty acid methyl esters can be prepared. The corresponding di- or oligoamides can be alkoxylated. These nonionic amphiphiles Compounds can be converted into anionic amphiphilic compounds be by z. B. the aforementioned compounds with SO₃ / inert gas (or oleum or chlorosulfonic acid), with polyphosphoric acid, with a Halogenacetic acid, with a sulton or with a taurine, and neutralized afterwards.
Bei den erfindungsgemäßen amphiphilen Verbindungen handelt es sich daher um Verbindungen der allgemeinen Formel IThe amphiphilic compounds according to the invention are therefore to compounds of the general formula I
wobei R¹, R², R³, X, Y und Z in der Formel I die im folgenden beschriebenen Bedeutungen haben: wherein R1, R2, R3, X, Y and Z in Formula I are those described below Have meanings:
R¹ und R³ stehen unabhängig voneinander für einen unverzweigten oder ver zweigten, gesättigten oder ungesättigten Kohlenwasserstoffrest mit 1 bis 22, vorzugsweise 7 bis 17, Kohlenstoffatomen.R¹ and R³ independently represent an unbranched or ver branched, saturated or unsaturated hydrocarbon radical with 1 to 22, preferably 7 to 17, carbon atoms.
Es seien als Substituenten R¹ und R³ im einzelnen die Reste Methyl, Ethyl, n-Propyl, n-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, n-Octyl, n-Nonyl, n-Decyl, n-Undecyl, n-Dodecyl, n-Tridecyl, n-Tetradecyl, n-Pentadecyl, n- Hexadecyl, n-Heptadecyl, n-Octadecyl, n-Nonadecyl, n-Eicosyl, n-Uneicosyl, n-Docosyl und ihre verzweigtkettigen Isomeren sowie die entsprechenden einfach, zweifach oder dreifach ungesättigten Reste genannt.The substituents R¹ and R³ are the radicals methyl, Ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n- Hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-uneicosyl, n-Docosyl and its branched chain isomers and the corresponding called single, double or triple unsaturated residues.
R² bedeutet einen Spacer, bestehend aus einer gegebenenfalls verzweigten Kette mit 2 bis 100 Kohlenstoffatomen, die gegebenenfalls je 1 bis 20 Sauerstoff- und/oder Stickstoffatome und/oder 1 bis 4 Schwefelatome und/oder 1 bis 3 Phosphoratome enthält, und die gegebenenfalls 1 bis 20 funktionelle Seitengruppen, wie z. B. Hydroxyl-, Carbonyl-, Carboxyl-, Amino- und/oder Acylaminogruppen, aufweist.R² means a spacer consisting of an optionally branched Chain with 2 to 100 carbon atoms, each optionally 1 to 20 Oxygen and / or nitrogen atoms and / or 1 to 4 sulfur atoms and / or contains 1 to 3 phosphorus atoms, and optionally 1 to 20 functional side groups, such as B. hydroxyl, carbonyl, carboxyl, Amino and / or acylamino groups.
Der Spacer R² bedeutet insbesondereThe spacer R² means in particular
- - unverzweigte oder verzweigte Alkylenketten der Formel II -CaH2a- (II)mit a = 2 bis 18, vorzugsweise a = 3 bis 6;unbranched or branched alkylene chains of the formula II -C a H 2a - (II) with a = 2 to 18, preferably a = 3 to 6;
- - unverzweigte oder verzweigte Alkenylenketten der Formel III -CbH2b-CH=CH-CcH2c- (III)mit b + c = 2 bis 16, wobei b und c jeweils größer als Null sind;unbranched or branched alkenylene chains of the formula III -C b H 2b -CH = CH-C c H 2c - (III) with b + c = 2 to 16, where b and c are each greater than zero;
- - unverzweigte oder verzweigte Alkinylenketten der Formel IV -CdH2d-C≡C-CeH2e- (IV)mit d + e = 2 bis 16, wobei d und e jeweils größer als Null sind, und wobei bei den Verbindungen gemäß den Formeln II bis IV der Spacer an einer beliebigen Stelle der Kette zusätzlich 1 bis 4 Carboxyl-, Amino- oder Acylaminogruppen enthalten kann; - Unbranched or branched alkynylene chains of the formula IV -C d H 2d -C≡CC e H 2e - (IV) with d + e = 2 to 16, where d and e are each greater than zero, and where the compounds according to Formulas II to IV of the spacers can additionally contain 1 to 4 carboxyl, amino or acylamino groups at any point in the chain;
-
- Alicyclen gemäß der Formel V
-CfH2f-cyclo C₆H₁₀-CgH2g- (V)mit f und g = je 1 bis 6
oder gemäß der Formel VI-3(4),8(9)-di(methylen)-tricyclo[5.2.1.02.6]decan- (VI)- Alicycles according to the formula V -C f H 2f -cyclo C₆H₁₀-C g H 2g - (V) with f and g = 1 to 6 each
or according to the formula VI-3 (4), 8 (9) -di (methylene) -tricyclo [5.2.1.0 2.6 ] decan- (VI) -
- gegebenenfalls substituierte Aromaten gemäß der Formel VII
-ChH2h-C₆R₄-(CiH2i-C₆R₄)j-CjH2j- (VII)oder gemäß der Formel VIII-ChH2h-C₁₀R₆-CjH2j- (VIII)mit h und j = je 0 bis 8 und i = 1 bis 8 und
mit R = unabhängig voneinander jeweils H oder C₁- bis C₄-Alkyl;- Optionally substituted aromatics according to the formula VII -C h H 2h -C₆R₄- (C i H 2i -C₆R₄) j -C j H 2j - (VII) or according to the formula VIII-C h H 2h -C₁₀R₆-C j H 2j - (VIII) with h and j = 0 to 8 and i = 1 to 8 and
with R = independently of one another each H or C₁- to C₄-alkyl; - - eine Kette mit funktionellen Seitengruppen, insbesondere eine Amino-, Acylamino-, Carbonyl- oder Carboxylfunktion.a chain with functional side groups, in particular an amino, Acylamino, carbonyl or carboxyl function.
Weiterhin können in dem Spacer R² zusätzlich je 1 bis 20, vorzugsweise 1 bis 12, Sauerstoff- und/oder Stickstoffatome und/oder gegebenenfalls 1 bis 4 Schwefelatome und/oder 1 bis 3 Phosphoratome enthalten sein.Furthermore, 1 to 20, preferably 1, each can additionally be in the spacer R 2 up to 12, oxygen and / or nitrogen atoms and / or optionally 1 up to 4 sulfur atoms and / or 1 to 3 phosphorus atoms.
R² hat damit weiterhin insbesondere die BedeutungR² therefore continues to be particularly important
-
- einer Verbindung gemäß der Formel IX
-CkH2k-CxRy-Z-CyRy-C₁H₂₁- (IX)mit k und l = je 0 bis 8, x = 6 und y = 4 oder
x = 10 und y = 6 oder x = 14 und y = 8, und
Z = 0, NH, NR¹, N-C(O)R¹, SO₂, wobei R¹ einen Kohlenwasserstoffrest mit 1 bis 22 Kohlenstoffatomen und R unabhängig voneinander jeweils H oder C₁-C₄-Alkyl bedeuten;- A compound of the formula IX -C k H 2k -C x R y -ZC y R y -C₁H₂₁- (IX) with k and l = 0 to 8, x = 6 and y = 4 or
x = 10 and y = 6 or x = 14 and y = 8, and
Z = 0, NH, NR¹, NC (O) R¹, SO₂, where R¹ is a hydrocarbon radical having 1 to 22 carbon atoms and R is independently H or C₁-C₄-alkyl; -
- einer Verbindung gemäß der Formel X
-CmH2m-(OCnH2n)p-CqH2q- (X)mit m = 1 bis 4, n = 2 bis 4, p = 1 bis 20, vorzugsweisse p = 1 bis
4, und q = 1 bis 4,
wobei auch gemischte Alkoxideinheiten auftreten können und dann die Reihenfolge der Alkoxideinheiten beliebig ist;- A compound according to the formula X -C m H 2m - (OC n H 2n ) p -C q H 2q - (X) with m = 1 to 4, n = 2 to 4, p = 1 to 20, preferably white p = 1 to 4, and q = 1 to 4,
mixed alkoxide units can also occur and the sequence of the alkoxide units is then arbitrary; -
- einer Verbindung gemäß der Formel XI
-CrH2r(RNCsH2s)t-CuH2u- (XI)oder gemäß der Formel XII-[CrH2r[RN-C(O)-NR]t-CuH2u]w- (XII)oder gemäß der Formel XIII-[CrH2r[RNC(O)CvH2vC(O)NR]t-CuH2u]w- (XIII)oder gemäß der Formel XIV-[CrH2r[RN-C(O)-CH=CH-C(O)-NR]t-CuH2u]w- (XIV)oder gemäß der Formel XV-[CrH2r[RNC(O)CxRyC(O)NR]t-CuH2u]w- (XV)mit r = 2 bis 4, s = 2 bis 4, t = 1 bis 20, vorzugsweise t = 1 bis
4, u = 2 bis 4, v = 0 bis 12, w = 1 bis 6, x = 6 und y = 4 oder
x = 10 und y = 0 oder
x = 14 und y = 8
mit R = unabhängig voneinander jeweils H oder C₁- bis C₄-Alkyl.- A compound according to the formula XI -C r H 2r (RNC s H 2s ) t -C u H 2u - (XI) or according to the formula XII- [C r H 2r [RN-C (O) -NR] t -C u H 2u ] w - (XII) or according to the formula XIII- [C r H 2r [RNC (O) C v H 2v C (O) NR] t -C u H 2u ] w - (XIII) or according to the formula XIV- [C r H 2r [RN-C (O) -CH = CH-C (O) -NR] t -C u H 2u ] w - (XIV) or according to the formula XV- [C r H 2r [RNC (O) C x R y C (O) NR] t -C u H 2u ] w - (XV) with r = 2 to 4, s = 2 to 4, t = 1 to 20, preferably t = 1 to 4, u = 2 to 4, v = 0 to 12, w = 1 to 6, x = 6 and y = 4 or
x = 10 and y = 0 or
x = 14 and y = 8
with R = independently of one another each H or C₁- to C₄-alkyl.
X und Y stehen unabhängig voneinander für Substituenten der Formel XVIX and Y independently of one another represent substituents of the formula XVI
-(C₂H₄O)α(C₃H₆O)βH (XVI)- (C₂H₄O) α (C₃H₆O) β H (XVI)
mit α = 0 bis 50, vorzugsweise α = 10 bis 30,
β = 0 bis 60, vorzugsweise β = 20 bis 40,
und α + β = 1 bis 100, vorzugsweise α + β = 10 bis 50,
wobei R² nicht C₂H₄ ist, wenn β = 0 ist,
und wobei die Alkoxideinheiten statistisch oder blockweise eingebunden
sind und die Reihenfolge beliebig ist;
oder für Substituenten der Formel XVIIwith α = 0 to 50, preferably α = 10 to 30,
β = 0 to 60, preferably β = 20 to 40,
and α + β = 1 to 100, preferably α + β = 10 to 50,
where R² is not C₂H₄ when β = 0,
and wherein the alkoxide units are included randomly or in blocks and the order is arbitrary;
or for substituents of the formula XVII
-(C₂H₄O)γ(C₃H₆O)δ-FR (XVII)- (C₂H₄O) γ (C₃H₆O) δ -FR (XVII)
mit jeweils γ = 0 bis 20, vorzugsweise γ = 0 bis 8,
δ = 0 bis 20, vorzugsweise δ = 0 bis 12,
und γ + δ = 1 bis 40, vorzugsweise γ + δ = 5 bis 20,
wobei FR für einen funktionellen Rest -CH₂-COOM, -SO₃M, -P(O(OM)₂,each with γ = 0 to 20, preferably γ = 0 to 8,
δ = 0 to 20, preferably δ = 0 to 12,
and γ + δ = 1 to 40, preferably γ + δ = 5 to 20,
where FR for a functional radical -CH₂-COOM, -SO₃M, -P (O (OM) ₂,
-O-C(O)-C₂H₃(SO₃M)-CO₂M′-O-C (O) -C₂H₃ (SO₃M) -CO₂M ′
oder -C₂H₄-SO₃M mit M, M′ = Alkali, Ammonium, Alkanolammonium oder
½ Erdalkali steht,
oder Substituenten der Formel XVIIIor -C₂H₄-SO₃M with M, M ′ = alkali, ammonium, alkanolammonium or ½ alkaline earth,
or substituents of the formula XVIII
-CH₂[CHO(C₂H₄O)ε(C₃H₆O)ηH]z-CH₂-O(C₂H₄O)µ(C₃H₆O)ρ-H (XVIII)-CH₂ [CHO (C₂H₄O) ε (C₃H₆O) η H] z -CH₂-O (C₂H₄O) µ (C₃H₆O) ρ -H (XVIII)
mit z = 3 bis 6, vorzugsweise z = 4
und ε bzw. µ = 0 bis 30, vorzugsweise ε bzw. µ = 0 bis 10,
und η bzw. ρ = 0 bis 30, vorzugsweise η bzw. ρ = 0 bis 10
und wobei die Alkoxideinheiten ebenfalls statistisch oder blockweise
eingebunden sind und die Reihenfolge beliebig ist.with z = 3 to 6, preferably z = 4
and ε or µ = 0 to 30, preferably ε or µ = 0 to 10,
and η or ρ = 0 to 30, preferably η or ρ = 0 to 10
and wherein the alkoxide units are also included randomly or in blocks and the order is arbitrary.
Der Oligomerisierungsgrad Z beträgt 1 bis 10, vorzugsweise Z = 1 bis 4, besonders bevorzugt Z = 1.The degree of oligomerization Z is 1 to 10, preferably Z = 1 to 4, particularly preferably Z = 1.
Der Alkoxylierungsgrad ist jeweils ein Mittelwert und kann jeden beliebigen, auch nicht ganzzahligen Wert in den angegebenen Grenzen einnehmen.The degree of alkoxylation is an average value and can be any also take a non-integer value within the specified limits.
Die erfindungsgemäße amphiphilen Verbindungen zeichnen sich meist durch extrem niedrige kritische Micellbildungskonzentrationen (CMC) und sehr niedrige Oberflächen- und Grenzflächenspannungen (z. B. gegen Paraffin) aus, was auf ihre besondere Struktur - wenigstens zwei hydrophile Gruppen und wenigstens zwei hydrophobe Gruppen - zurückgeführt werden muß. Darüber hinaus weisen die meisten von ihnen ein recht hohes hydrophiles Suspendiervermögen auf, das etwa auf halbem Wege zwischen dem konventio neller Tenside und dem des Pentanatriumtripolyphosphats liegt. Einige dieser Verbindungen sind extrem schnelle Netzmittel.The amphiphilic compounds according to the invention are usually characterized by extremely low critical micelle levels (CMC) and very low surface and interfacial tensions (e.g. against paraffin) from what is due to their special structure - at least two hydrophilic groups and at least two hydrophobic groups - must be recycled. In addition, most of them are quite hydrophilic Suspending capacity that is about halfway between the convention neller surfactants and that of pentasodium tripolyphosphate. Some these connections are extremely fast wetting agents.
Die amphiphilen Verbindungen gemäß dieser Erfindung eignen sich insbesondere als Emulgatoren, Demulgatoren, Detergenzien, Dispergatoren und Hydrotropica in Industrie und Haushalt, beispielsweise auf den Gebieten Metallbearbeitung, Erzgewinnung, Oberflächenveredelung, Waschen und Reinigen, Kosmetik, Medizin und Nahrungsmittelverarbeitung und -zuberei tung.The amphiphilic compounds according to this invention are particularly suitable as emulsifiers, demulsifiers, detergents, dispersants and Hydrotropica in industry and household, for example in the fields Metalworking, ore extraction, surface finishing, washing and Cleaning, cosmetics, medicine and food processing and preparation tung.
Hierbei können sie mit allen gängigen anionischen, nichtionischen, katio nischen und ampholytischen grenzflächenaktiven Substanzen kombiniert werden. Als Beispiele für nichtionische grenzflächenaktive Substanzen, die für eine Kombination eingesetzt werden können, seien genannt: Fettsäure glyceride, Fettsäurepolyglyceride, Fettsäureester, Ethoxylate höherer Alkohole, Polyoxyethylenfettsäureglyceride, Polyoxyethylenpropylenglykol fettsäureester, Polyoxyethylensorbitanfettsäureester, Polyoxyethylen-Rhi zinusöl- oder gehärtete Rhizinusöl-Derivate, Polyoxyethylenlanolinderi vate, Polyoxyethylenfettsäureamide, Polyoxyethylenalkylamine, Alkanolamine, Alkylaminoxide, Derivate von Eiweißhydrolysaten, Hydroxymischether, Alkylpolyglycoside und Alkylglucamide.You can use all common anionic, nonionic, katio African and ampholytic surfactants can be combined. As examples of nonionic surfactants, the can be used for a combination, may be mentioned: fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, Polyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene Rhi castor oil or hardened castor oil derivatives, polyoxyethylene lanolinderi vate, polyoxyethylene fatty acid amides, polyoxyethylene alkyl amines, alkanol amines, Alkylamine oxides, derivatives of protein hydrolyzates, hydroxy mixed ethers, Alkyl polyglycosides and alkyl glucamides.
Als Beispiele für anionische grenzflächenaktive Substanzen, die für Kom binationen eingesetzt werden können, seien genannt: Seifen, Ethercarbon säure und deren Salze, Alkylsulfonate, α-Olefinsulfonate, Sulfonate höherer Fettsäureester, höhere Alkoholsulfate, Alkoholethersulfate, Hy droxymischethersulfate, Salze von Phosphatestern, Tauride, Isethionate, lineare Alkylbenzolsulfonate, Cumolsulfonat, Alkylarylsulfonate, Sulfate der Polyoxyethylenfettsäureamide und Salze von Acylaminosäuren.As examples of anionic surface-active substances which are suitable for com combinations can be used: soaps, ether carbon acid and its salts, alkyl sulfonates, α-olefin sulfonates, sulfonates higher Fatty acid esters, higher alcohol sulfates, alcohol ether sulfates, hy droxy mixed ether sulfates, salts of phosphate esters, taurides, isethionates, linear alkyl benzene sulfonates, cumene sulfonate, alkyl aryl sulfonates, sulfates of polyoxyethylene fatty acid amides and salts of acylamino acids.
Als Beispiele für kationische gängige grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien genannt: Alkytri methylammoniumsalze, Dialkylmethylammoniumsalze, Alkyldimethylbenzyl ammoniumsalze, Alkylpridiniumsalze, Alkylisochinoliniumsalze, Benzetho niumchloride und kationische Acylaminosäurederivate.As examples of common cationic surfactants that can be used for combinations: Alkytri methylammonium salts, dialkylmethylammonium salts, alkyldimethylbenzyl ammonium salts, alkylpridinium salts, alkylisoquinolinium salts, benzetho nium chlorides and cationic acylamino acid derivatives.
Als Beispiele für ampholytische grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien genannt: Aminosäuren, Betaine, Sulfobetaine, Imidazolinderivate, Sojaöllipide und Lecithin. As examples of ampholytic surfactants used for Combinations that can be used include: amino acids, Betaines, sulfobetaines, imidazoline derivatives, soybean oil lipids and lecithin.
Darüber hinaus können die erfindungsgemäßen amphiphilen Verbindungen auch für sich miteinander kombiniert werden.In addition, the amphiphilic compounds according to the invention can also can be combined with each other.
Den erfindungsgemäßen amphiphilen Verbindungen können ebenfalls gängige Additive zugesetzt werden. Solche Additive werden speziell für eine For mulierung ausgewählt und umfassen üblicherweise anorganische Salze, wie Natriumchlorid und -sulfat, sowie Builder, Hydrotropica, UV-Absorber, Weichmacher, Chelatbildner, Viskositätsmodifizierer und Riechstoffe.The amphiphilic compounds according to the invention can also be common Additives are added. Such additives are specifically for a For mulation selected and usually include inorganic salts such as Sodium chloride and sulfate, as well as builders, hydrotropics, UV absorbers, Plasticizers, chelating agents, viscosity modifiers and fragrances.
Die oben genannten Verbindungen lassen sich nach bekannten Methoden her stellen: Die Di- oder Oligoamine werden mit je einem Äquivalent Fettsäure oder Fettsäuremethylester pro freier NH-Funktion bei erhöhten Temperaturen (80 bis 180°C) optional in Gegenwart eines Katalysators umgesetzt, wobei das entstehende Wasser oder das Methanol unter Vakuum entfernt wird. An schließend wird bei Temperaturen von 130 bis 190°C in Gegenwart eines basischen Katalysators alkoxyliert. Die flüssigen oder bei niedrigen Tem peraturen erweichenden Produkte können anschließend mit SO₃/Inertgas (Oleum oder Chlorsulfonsäure) oder Polyphosphorsäure oder mit einer Halo genessigsäure, einem Sulton oder mit Isethionsäure umgesetzt und mit wäßrigen Alkali- oder Erdalkalihydroxiden oder wäßrigem Ammoniak oder Alka nolaminen neutralisiert werden. Bei Bedarf werden die Produkte in wäßriger Lösung mit Wasserstoffperoxid (0,1 bis 2,0%, bezogen auf Feststoff) gebleicht.The above-mentioned compounds can be prepared by known methods places: The di- or oligoamines are each with one equivalent of fatty acid or fatty acid methyl ester per free NH function at elevated temperatures (80 to 180 ° C) optionally implemented in the presence of a catalyst, wherein the water or methanol formed is removed under vacuum. On concluding at temperatures from 130 to 190 ° C in the presence of a alkoxylated basic catalyst. The liquid or at low tem Temperature softening products can then with SO₃ / inert gas (Oleum or chlorosulfonic acid) or polyphosphoric acid or with a halo genacetic acid, a sulton or reacted with isethionic acid and with aqueous Alkali or alkaline earth metal hydroxides or aqueous ammonia or Alka nolamines are neutralized. If necessary, the products become more watery Solution with hydrogen peroxide (0.1 to 2.0%, based on solids) bleached.
Folgende Beispiele sollen die Erfindung erläutern, sie jedoch nicht dar auf einschränken. Alle Angabe in Prozent sind Gewichtsprozent.The following examples are intended to illustrate the invention, but not to illustrate it restrict to. All percentages are percentages by weight.
In einem 1-l-Vierhalskolben mit Rührer, Thermometer, Wasserauskreiser und angeschlossenem Rückflußkühler werden 91,8 g Ethylendiamin mit 441,5 g Octan- und Decansäuremethylestergemisch (1 : 1) gemischt und auf 120 bis 140°C erhitzt. Innerhalb von 7 Stunden werden 72,3 ml Methanol entfernt und die Reaktion anschließend beendet. Die Reinheit der drei aus dem Homologengemisch entstandenen Diamide wird mittels ¹³C-NMR überprüft und liegt bei <99 mol-%, Ausbeute 447,2 g (85% d. Th.).In a 1 liter four-necked flask with stirrer, thermometer, water separator and connected reflux condenser are 91.8 g of ethylenediamine with 441.5 g Mixture of octanoic acid and methyl decanoate (1: 1) and make up to 120 to Heated 140 ° C. 72.3 ml of methanol are removed within 7 hours and the reaction then ended. The purity of the three from the Homologous mixture of diamides is checked by means of 13 C-NMR and is <99 mol%, yield 447.2 g (85% of theory).
170,0 g des Diamidgemisches werden mit 150 ml Testbenzin gemischt und
mit 1,1 g festen Kaliumhydroxids versetzt. Bei 160°C wird das Gemisch
mit 220 g Ethylenoxid innerhalb von 6 Stunden umgesetzt. Der Katalysator
wird mit Milchsäure neutralisiert und das ausfallende Kaliumsalz sowie
eventuell nicht umgesetztes Diamid abfiltriert. Anhand der Auswaage wird
auf kompletten Umsatz des Ethylenoxids geprüft und per ¹³C-NMR das Ver
hältnis Ethylenoxid zum Restmolekül bestimmt: 10 EO-Einheiten pro Restmolekül,
Ausbeute: 390 g (quantitativ), keine verbleibenden N-H-Funktionen im
Produktgemisch laut IR.170.0 g of the diamide mixture are mixed with 150 ml white spirit and 1.1 g solid potassium hydroxide are added. At 160 ° C, the mixture is reacted with 220 g of ethylene oxide within 6 hours. The catalyst is neutralized with lactic acid and the precipitated potassium salt and any unreacted diamide are filtered off. The balance is used to check the complete conversion of the ethylene oxide and the ratio of ethylene oxide to the residual molecule is determined by 13 C-NMR: 10 EO units per residual molecule,
Yield: 390 g (quantitative), no remaining NH functions in the product mixture according to IR.
Zu einem Gemisch aus 117,7 g Chlorsulfonsäure und 60,2 g Essigsäure werden
218,5 g des erhaltenen Ethoxylates in 300 ml Dichlormethan so zuge
tropft, daß die Temperatur 5°C nicht übersteigt. Anschließend wird bei
Raumtemperatur 3 Stunden gerührt (laut Kontrolle per Dünnschichtchromato
graphie ist das Ethoxylat vollständig umgesetzt). Es wird mit 2-normaler
Natriumcarbonatlösung neutralisiert und mit gesättigter Natriumhydrogen
carbonatlösung verdünnt. Mit n-Butanol wird das Produkt extrahiert und
anschließend der Alkohol entfernt.
Die Reinheitskontrolle erfolgt per Dünnschichtchromatographie und NMR.
Ausbeute: 96,8 g (36% d. Th.), Reinheit: 90%; charakteristische ¹³C-NMR
Daten (DMSO-D₆): 171,8 ppm, 69,2 ppm, 68,7 ppm, 67,8 ppm, 64,6 ppm,
62,3 ppm, 32,9 ppm, 30,7 ppm, 27,9-28,3 ppm, 24 ppm (breit), 21,9 ppm,
13,1 ppm;
CMC: 0,011 g/l, λCMC = 30 mN/m (in VE-Wasser, 20°C), λParaffin =
2,5 mN/m (0,1 g WAS in VE-Wasser, 20°C).218.5 g of the ethoxylate obtained in 300 ml of dichloromethane are added dropwise to a mixture of 117.7 g of chlorosulfonic acid and 60.2 g of acetic acid in such a way that the temperature does not exceed 5 ° C. The mixture is then stirred at room temperature for 3 hours (according to control by thin layer chromatography, the ethoxylate is completely converted). It is neutralized with 2 normal sodium carbonate solution and diluted with saturated sodium bicarbonate solution. The product is extracted with n-butanol and then the alcohol is removed.
The purity is checked by thin layer chromatography and NMR.
Yield: 96.8 g (36% of theory), purity: 90%; characteristic 13 C-NMR data (DMSO-D-): 171.8 ppm, 69.2 ppm, 68.7 ppm, 67.8 ppm, 64.6 ppm, 62.3 ppm, 32.9 ppm, 30.7 ppm , 27.9-28.3 ppm, 24 ppm (broad), 21.9 ppm, 13.1 ppm;
CMC: 0.011 g / l, λ CMC = 30 mN / m (in demineralized water, 20 ° C), λ paraffin = 2.5 mN / m (0.1 g WAS in demineralized water, 20 ° C).
Die Reaktion wird analog zum Beispiel 1 durchgeführt:
Es wird dasselbe Diamidgemsich wie in Beispiel 1 hergestellt.
Ethoxylierung: 170 g Diamidgemisch, 150 ml Testbenzin, 440 g Ethylenoxid,
1,1 g KOH, laut NMR 20 EO-Einheiten pro Restmolekül, Ausbeute: 610 g
(quantitativ).
Sulfatierung:
217,5 g Ethoxylat, 78,8 g Chlorsulfonsäure, 40,3 g Essigsäure,
Ausbeute: 123,7 g (50% d. Th.), Reinheit: 90%, charakteristische ¹³C-
NMR Daten (DMSO-D₆): 172,0 ppm, 69,4 ppm, 69,1 ppm, 65,2 ppm, 28,5 ppm
(breit), 21,1 ppm, 13,4 ppm; CMC: 0,13 g/l, λCMC = 33 mN/m (VE-Wasser,
20°C), λParaffin = 15,5 mN/m (0,1 g WAS in VE-Wasser, 20°C.The reaction is carried out analogously to Example 1:
The same diamide is prepared as in Example 1.
Ethoxylation: 170 g diamide mixture, 150 ml white spirit, 440 g ethylene oxide, 1.1 g KOH, according to NMR 20 EO units per residual molecule, yield: 610 g (quantitative).
Sulfation: 217.5 g ethoxylate, 78.8 g chlorosulfonic acid, 40.3 g acetic acid, yield: 123.7 g (50% of theory), purity: 90%, characteristic ¹³C-NMR data (DMSO-D-) : 172.0 ppm, 69.4 ppm, 69.1 ppm, 65.2 ppm, 28.5 ppm (broad), 21.1 ppm, 13.4 ppm; CMC: 0.13 g / l, λ CMC = 33 mN / m (deionized water, 20 ° C), λ paraffin = 15.5 mN / m (0.1 g WAS in deionized water, 20 ° C.
Die Reaktion wird analog zu Beispiel 1 durchgeführt:
116,2 g Hexamethylendiamin, 344,0 g Octan- und Decansäuregemisch (1 : 1),
0,2 g ZnO,
Reaktionszeit: 7 Stunden, Reaktionstemperatur: 140 bis 145°C, Ausbeute
an Diamidgemisch: 465 g, Reinheit: <95%;
Ethoxylierung: 170 g Diamidgemisch, 150 ml Testbenzin, 292 g Ethylenoxid,
1,1 g KOH,
Ausbeute Ethoxylat: 370 g, 8 EO-Einheiten pro Restmolekül;
Sufatierung: analog Beispiel 1
Ausbeute: 105,4 g (62% d. Th.), Reinheit: 92%, charakteristische
¹³C-NMR Daten (DMSO-D₆): 173,4 ppm (breit), 70,4 ppm, 69,3 ppm, 68,9 ppm,
68,1 ppm, 33,1 ppm, 28 bis 29 ppm (breit), 22,0 ppm, 13,0 ppm; CMC: 0,016 g/l,
λCMC = 28,5 mN/m (in VE-Wasser, 20°C), λParaffin = 3,0 mN/m (0,1 g
WAS in VE-Wasser, 20°C).The reaction is carried out analogously to Example 1:
116.2 g hexamethylenediamine, 344.0 g octanoic and decanoic acid mixture (1: 1), 0.2 g ZnO,
Reaction time: 7 hours, reaction temperature: 140 to 145 ° C., yield of diamide mixture: 465 g, purity: <95%;
Ethoxylation: 170 g diamide mixture, 150 ml white spirit, 292 g ethylene oxide, 1.1 g KOH,
Yield ethoxylate: 370 g, 8 EO units per residual molecule;
Sufation: analogous to example 1
Yield: 105.4 g (62% of theory), purity: 92%, characteristic 13 C-NMR data (DMSO-D₆): 173.4 ppm (broad), 70.4 ppm, 69.3 ppm, 68 , 9 ppm, 68.1 ppm, 33.1 ppm, 28 to 29 ppm (broad), 22.0 ppm, 13.0 ppm; CMC: 0.016 g / l, λ CMC = 28.5 mN / m (in demineralized water, 20 ° C), λ paraffin = 3.0 mN / m (0.1 g WAS in demineralized water, 20 ° C ).
Claims (19)
R² einen Spacer und
X und Y unabhängig voneinander funktionelle Gruppen bedeuten und der Oligomerisierungsgrad Z = 1 bis 10 beträgt.1. Amphiphilic compounds of the formula I. in which R¹ and R³ independently of one another are a hydrocarbon radical having 1 to 22 carbon atoms,
R² a spacer and
X and Y are independently functional groups and the degree of oligomerization Z = 1 to 10.
daß die Kohlenwasserstoffreste R¹ und R³ unverzweigt oder verzweigt, gesättigt oder ungesättigt sind,
der Spacer R² eine gegebenenfalls verzweigte Kette mit 2 bis 100 Koh lenstoffatome, die gegebenenfalls je 1 bis 20 Sauerstoff- und/oder Stickstoffatome und/oder 1 bis 4 Schwefelatome und/oder 1 bis 3 Phos phoratome enthält und die gegebenenfalls 1 bis 20 funktionelle Sei tengruppen aufweist, bedeutet und
X und Y unabhängig voneinander für funktionelle Gruppen, die gegebe nenfalls alkoxyliert sind, steht.2. Amphiphilic compounds according to claim 1, characterized in that
that the hydrocarbon radicals R¹ and R³ are unbranched or branched, saturated or unsaturated,
the spacer R² is an optionally branched chain with 2 to 100 carbon atoms, optionally containing 1 to 20 oxygen and / or nitrogen atoms and / or 1 to 4 sulfur atoms and / or 1 to 3 phosphorus atoms and optionally 1 to 20 functional groups has ten groups means and
X and Y independently of one another represent functional groups which are optionally alkoxylated.
oder aus einer unverzweigten oder verzweigten Alkenylenkette der Formel III-CbH2b-CH=CH-CcH2c- (III)mit b + c = 2 bis 16, wobei b und c jeweils größer als Null sind,
oder aus einer unverzweigten oder verzweigten Alkinylenkette der Formel IV-CdH2d-C≡C-CeH2e- (IV)mit d + e = 2 bis 16, wobei d und e jeweils größer als Null sind, und wobei bei den Verbindungen gemäß den Formeln II bis IV der Spacer an einer beliebigen Stelle der Kette zusätzlich 1 bis 4 Carbonyl-, Amino- oder Acylaminogruppen enthalten kann,
besteht.5. Amphiphilic compounds according to claims 1 to 4, characterized in that R² is a spacer which consists of an unbranched or branched alkylene chain of the formula II -C a H 2a - (II) with a = 2 to 18, preferably a = 3 until 6,
or from an unbranched or branched alkenylene chain of the formula III-C b H 2b -CH = CH-C c H 2c - (III) with b + c = 2 to 16, where b and c are each greater than zero,
or from an unbranched or branched alkynylene chain of the formula IV-C d H 2d -C≡CC e H 2e - (IV) with d + e = 2 to 16, where d and e are each greater than zero, and where the compounds according to formulas II to IV, the spacer can additionally contain 1 to 4 carbonyl, amino or acylamino groups at any point in the chain,
consists.
oder gemäß der Formel VI-3(4),8(9)-di(methylen)-tricyclo[5.2.1.02.6]decan- (VI)besteht. 6. Amphiphilic compounds according to claims 1 to 4, characterized in that R² is a spacer consisting of alicyclene according to the formula V -C f H 2f -cyclo C₆H₁₀-C g H 2g - (V) with f and g = each 1 to 6
or according to the formula VI-3 (4), 8 (9) -di (methylene) -tricyclo [5.2.1.0 2.6 ] decane (VI).
mit R = unabhängig voneinander jeweils H oder C₁- bis C₄-Alkyl
besteht.7. Amphiphilic compounds according to Claims 1 to 4, characterized in that R² is a spacer which consists of optionally substituted aromatics according to the formula VII -C h H 2h -C₆R₄- (C i H 2i -C₆R₄) j -C j H 2j - (VII) or according to the formula VIII-C h H 2h -C₁₀R₆-C j H 2j - (VIII) with h and j = 0 to 8 and i = 1 to 8 and
with R = independently of one another each H or C₁- to C₄-alkyl
consists.
x = 10 und y = 6 oder x = 14 und y = 8, und
Z = O, CO, NH, NR¹, N-C(O)R¹, SO₂, wobei R¹ für einen Kohlenwasser stoffrest mit 1 bis 22 Kohlenstoffatomen und R unabhängig vonein ander jeweils H oder C₁- bis C₄-Alkyl steht,
bedeutet. 10. Amphiphilic compounds according to claim 9, characterized in that R² is a spacer of the formula (IX) -C k H 2k -C x R y -ZC x R y -C₁H₂₁- (IX) with k and l = 0 to each 8, x = 6 and y = 4 or
x = 10 and y = 6 or x = 14 and y = 8, and
Z = O, CO, NH, NR¹, NC (O) R¹, SO₂, where R¹ is a hydrocarbon radical having 1 to 22 carbon atoms and R independently of one another is H or C₁- to C₄-alkyl,
means.
wobei auch gemischte Alkoxideinheiten auftreten können und dann die Reihenfolge der Alkoxideinheiten beliebig ist,
bedeutet.11. Amphiphilic compounds according to claim 9, characterized in that R² is a spacer according to the formula X -C m H 2m - (C n H 2n O) p -C q H 2q - (X) with m = 1 to 4, n = 2 to 4, p = 1 to 20, preferably white p = 1 to 4, and q = 1 to 4,
mixed alkoxide units can also occur and the sequence of the alkoxide units is then arbitrary,
means.
x = 10 und y = 0 oder
x = 14 und y = 8
mit R = unabhängig voneinander jeweils H oder C₁- bis C₄-Alkyl,
bedeutet. 12. Amphiphilic compounds according to claim 9, characterized in that R² is a spacer according to the formula XI -C r H 2r (RNC s H 2s ) t -C u H 2u - (XI) or according to the formula XII- [C r H 2r [RN-C (O) -NR] t -C u H 2u ] w - (XII) or according to the formula XIII- [C r H 2r [RNC (O) C v H 2v C (O) NR] t -C u H 2u ] w - (XIII) or according to the formula XIV- [C r H 2r [RN-C (O) -CH = CH-C (O) -NR] t -C u H 2u ] w - (XIV) or according to the formula XV- [C r H 2r [RNC (O) C x R y C (O) NR] t -C u H 2u ] w - (XV) with r = 2 to 4, s = 2 to 4, t = 1 to 20, preferably t = 1 to 4, u = 2 to 4, v = 0 to 12, w = 1 to 6, x = 6 and y = 4 or
x = 10 and y = 0 or
x = 14 and y = 8
with R = independently of one another in each case H or C₁- to C₄-alkyl,
means.
β = 0 bis 60, vorzugsweise β = 20 bis 40,
und α + β = 1 bis 100, vorzugsweise α + β = 10 bis 50,
wobei R² nicht C₂H₄ ist, wenn β = 0 ist,
bedeuten und wobei die Alkoxideinheiten statistisch oder blockweise eingebunden sind und die Reihenfolge beliebig ist.13. Amphiphilic compounds according to claims 1 to 12, characterized in that X and Y independently of one another the substituents of the formula XVI - (C₂H₄O) α (C₃H₆O) β H (XVI) with α = 0 to 50, preferably α = 10 to 30,
β = 0 to 60, preferably β = 20 to 40,
and α + β = 1 to 100, preferably α + β = 10 to 50,
where R² is not C₂H₄ when β = 0,
mean and wherein the alkoxide units are included randomly or in blocks and the order is arbitrary.
δ = 0 bis 20, vorzugsweise δ = 0 bis 12,
und γ + δ = 1 bis 40, vorzugsweise γ + δ = 5 bis 20,
wobei FR für einen funktionellen Rest -CH₂-COOM, -SO₃M, -P(O(OM)₂,-O-C(O)-C₂H₃(SO₃M)-CO₂M′oder -C₂H₄-SO₃M mit M, M′ = Alkali, Ammonium, Alkanolammonium oder ½ Erdalkali steht,
oder Substituenten der Formel XVIII-CH₂[CHO(C₂H₄O)ε(C₃H₆O)ηH]z-CH₂-O(C₂H₄O)µ(C₃H₆O)ρ-H (XVIII)mit z = 3 bis 6, vorzugsweise z = 4
und ε bzw. µ = 0 bis 30, vorzugsweise ε bzw. µ = 0 bis 10,
und η bzw. ρ = 0 bis 30, vorzugsweise η bzw. ρ = 0 bis 10
und wobei die Alkoxideinheiten statistisch oder blockweise eingebunden sind und die Reihenfolge beliebig ist, bedeuten.14. Amphiphilic compounds according to claims 1 to 12, characterized in that X and Y independently of one another substituents of the formula XVII - (C₂H₄O) γ (C₃H₆O) δ -FR (XVII) each with γ = 0 to 20, preferably γ = 0 till 8,
δ = 0 to 20, preferably δ = 0 to 12,
and γ + δ = 1 to 40, preferably γ + δ = 5 to 20,
where FR for a functional radical -CH₂-COOM, -SO₃M, -P (O (OM) ₂, -OC (O) -C₂H₃ (SO₃M) -CO₂M′or -C₂H₄-SO₃M with M, M ′ = alkali, ammonium , Alkanolammonium or ½ alkaline earth,
or substituents of the formula XVIII-CH₂ [CHO (C₂H₄O) ε (C₃H₆O) η H] z -CH₂-O (C₂H₄O) µ (C₃H₆O) ρ -H (XVIII) with z = 3 to 6, preferably z = 4
and ε or µ = 0 to 30, preferably ε or µ = 0 to 10,
and η or ρ = 0 to 30, preferably η or ρ = 0 to 10
and where the alkoxide units are included randomly or in blocks and the order is arbitrary.
Priority Applications (12)
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DE4440328A DE4440328A1 (en) | 1994-11-11 | 1994-11-11 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides |
AU35678/95A AU689649B2 (en) | 1994-11-11 | 1995-09-15 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides |
AT95932759T ATE210493T1 (en) | 1994-11-11 | 1995-09-15 | AMPHIPHILIC COMPOUNDS WITH AT LEAST TWO HYDROPHILES AND AT LEAST TWO HYDROPHOBIC GROUPS BASED ON AMIDES |
BR9509636A BR9509636A (en) | 1994-11-11 | 1995-09-15 | Amphiphilic compounds with at least two hydrophilic groups and at least two hydrophobic groups based on amides |
ES95932759T ES2171194T3 (en) | 1994-11-11 | 1995-09-15 | AMPHIFILIC COMPOUNDS WITH AT LEAST TWO HYDROPHILE GROUPS AND AT LEAST TWO HYDROPHOBE GROUPS BASED ON AMIDAS. |
JP51566496A JP4390021B2 (en) | 1994-11-11 | 1995-09-15 | Amide-based amphiphilic compounds having at least two hydrophilic groups and at least two hydrophobic groups |
US08/817,930 US6342625B1 (en) | 1994-11-11 | 1995-09-15 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides |
EP95932759A EP0804279B1 (en) | 1994-11-11 | 1995-09-15 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides |
CN95197305A CN1090051C (en) | 1994-11-11 | 1995-09-15 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides |
DE59509951T DE59509951D1 (en) | 1994-11-11 | 1995-09-15 | AMPHIPHILE COMPOUNDS WITH AT LEAST TWO HYDROPHILES AND AT LEAST TWO HYDROPHOBIC GROUPS BASED ON AMIDES |
PCT/EP1995/003635 WO1996014926A1 (en) | 1994-11-11 | 1995-09-15 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on amides |
TR95/01368A TR199501368A2 (en) | 1994-11-11 | 1995-11-03 | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups on the basis of amides. |
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DE59509951T Expired - Lifetime DE59509951D1 (en) | 1994-11-11 | 1995-09-15 | AMPHIPHILE COMPOUNDS WITH AT LEAST TWO HYDROPHILES AND AT LEAST TWO HYDROPHOBIC GROUPS BASED ON AMIDES |
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US (1) | US6342625B1 (en) |
EP (1) | EP0804279B1 (en) |
JP (1) | JP4390021B2 (en) |
CN (1) | CN1090051C (en) |
AT (1) | ATE210493T1 (en) |
AU (1) | AU689649B2 (en) |
BR (1) | BR9509636A (en) |
DE (2) | DE4440328A1 (en) |
ES (1) | ES2171194T3 (en) |
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WO1998000392A1 (en) * | 1996-06-28 | 1998-01-08 | Rwe-Dea Aktiengesellschaft Für Mineraloel Und Chem | Process for preparing mono-, di- or oligoamide alkoxylates |
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JPS6096695A (en) | 1983-10-31 | 1985-05-30 | 三洋化成工業株式会社 | Detergent composition |
EP0258923B1 (en) | 1986-09-02 | 1993-10-06 | Akzo Nobel N.V. | Fabric softening composition and detergent-composition comprising the same |
GB9018157D0 (en) * | 1990-08-17 | 1990-10-03 | Procter & Gamble | Detergent compositions |
JP2907517B2 (en) | 1990-09-12 | 1999-06-21 | 鐘紡株式会社 | 2- or 3-chain bihydrophilic compound |
US5160450A (en) | 1990-12-05 | 1992-11-03 | Lion Corporation | Surface-active agents having two hydrophobic chains and two hydrophilic groups |
DE4227894A1 (en) | 1992-08-22 | 1994-02-24 | Basf Ag | Removal of organic components from pH-sensitive surfactant-contg. effluent - by treating with acid and separating the organic phase |
SE500923C2 (en) | 1993-10-21 | 1994-10-03 | Berol Nobel Ab | Use of an amphoteric surfactant as a friction reducing agent in an aqueous liquid system |
WO1995019955A1 (en) * | 1994-01-25 | 1995-07-27 | The Procter & Gamble Company | Gemini polyether fatty acid amides and their use in detergent compositions |
DE19505368A1 (en) * | 1995-02-17 | 1996-08-22 | Huels Chemische Werke Ag | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on dicarboxylic acid diamides |
-
1994
- 1994-11-11 DE DE4440328A patent/DE4440328A1/en not_active Withdrawn
-
1995
- 1995-09-15 BR BR9509636A patent/BR9509636A/en not_active IP Right Cessation
- 1995-09-15 WO PCT/EP1995/003635 patent/WO1996014926A1/en active IP Right Grant
- 1995-09-15 US US08/817,930 patent/US6342625B1/en not_active Expired - Lifetime
- 1995-09-15 ES ES95932759T patent/ES2171194T3/en not_active Expired - Lifetime
- 1995-09-15 EP EP95932759A patent/EP0804279B1/en not_active Expired - Lifetime
- 1995-09-15 JP JP51566496A patent/JP4390021B2/en not_active Expired - Fee Related
- 1995-09-15 DE DE59509951T patent/DE59509951D1/en not_active Expired - Lifetime
- 1995-09-15 AT AT95932759T patent/ATE210493T1/en not_active IP Right Cessation
- 1995-09-15 AU AU35678/95A patent/AU689649B2/en not_active Ceased
- 1995-09-15 CN CN95197305A patent/CN1090051C/en not_active Expired - Lifetime
- 1995-11-03 TR TR95/01368A patent/TR199501368A2/en unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5710121A (en) * | 1995-12-21 | 1998-01-20 | Rhone-Poulenc Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
WO1997040124A1 (en) * | 1996-04-23 | 1997-10-30 | RWE-DEA Aktiengesellschaft für Mineraloel und Chemie | Use of anionic gemini tensides in formulations for washing, cleaning and body care agents |
WO1998000392A1 (en) * | 1996-06-28 | 1998-01-08 | Rwe-Dea Aktiengesellschaft Für Mineraloel Und Chem | Process for preparing mono-, di- or oligoamide alkoxylates |
US6211409B1 (en) | 1996-06-28 | 2001-04-03 | Rwe-Dea Aktiengesellschaft Fuer Mineraloel Und Chemie | Process for preparing mono-, Di- or oligoamide alkoxylates |
WO1998015345A1 (en) * | 1996-10-04 | 1998-04-16 | Rhodia Inc. | Detergent compositions containing low concentration levels of gemini surfactants |
US6121222A (en) * | 1996-12-27 | 2000-09-19 | Rhodia Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
Also Published As
Publication number | Publication date |
---|---|
ES2171194T3 (en) | 2002-09-01 |
AU689649B2 (en) | 1998-04-02 |
EP0804279A1 (en) | 1997-11-05 |
WO1996014926A1 (en) | 1996-05-23 |
JP4390021B2 (en) | 2009-12-24 |
EP0804279B1 (en) | 2001-12-12 |
CN1172439A (en) | 1998-02-04 |
ATE210493T1 (en) | 2001-12-15 |
US6342625B1 (en) | 2002-01-29 |
DE59509951D1 (en) | 2002-01-24 |
JPH10511932A (en) | 1998-11-17 |
TR199501368A2 (en) | 1996-06-21 |
CN1090051C (en) | 2002-09-04 |
AU3567895A (en) | 1996-06-06 |
BR9509636A (en) | 1997-10-14 |
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